


Homework Help

by lydslibrary



Category: Supernatural
Genre: Blindfolds, Dean Winchester Smut, Dirty Talk, Dom!Dean Winchester, F/M, Fingering, Oral Sex, Rough Sex, Sex, Stress Relief, Vibrator, sub!Reader
Language: English
Status: Completed
Published: 2020-09-19
Updated: 2020-10-14
Packaged: 2021-03-08 03:54:59
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 5,505
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26549332
Author URL: https://archiveofourown.org/users/lydslibrary/pseuds/lydslibrary
Summary: You're having trouble focusing on your homework and Dean has an idea about how to help you concentrate.
Relationships: Dean Winchester/Reader
Comments: 5
Kudos: 54





	1. Chapter 1

You jumped as you heard a knock at the door. You had been sitting at your desk, racking your brain over an essay that you had to write for one of your classes since you woke up… which was five hours ago. Judging by how startled you were from a gentle knock at the door, you must have zoned in completely to what you were doing, tuning out any outside noises. You let out a sigh and rubbed your eyes which were beginning to burn from the hours that you had been staring at your laptop.

“Come in,” you groaned, leaning back in your chair, thankful for the brief moment of distraction.

“You okay sweetheart? You’ve been in here for hours,” you heard your favorite person’s voice ask. You smiled softly and turned your body so you were now sitting sideways, your arm draped over the back of your chair. Your eyes got wide when you saw that your favorite person in the world was carrying a take-out bag from your favorite restaurant in the world.

“Dean Winchester, you are an angel,” you beamed as you made grabby hands at the bag that he was holding. He chuckled that deep chuckle of his and walked towards you, handing you the bag and bending over to give you a quick kiss on the lips.

“I figured you’d be forgetting to eat today. How’s it going?”

You placed the take-out next to your laptop and glanced at the word document open on the screen; only three out of eight pages written so far. “I swear I’ve just been zoning in an out of consciousness. I haven’t written anything in almost two hours, I’ve just been staring at the damn screen. Go back to school, they said. It’ll be fun, they said,” you sighed. You leaned your head against Dean’s stomach as he stood behind the chair and he ran his fingers through your hair.

“I hate seeing you so stressed,” he said gently, his free hand beginning to massage one of your shoulders.

“I hate being so stressed,” you groaned, letting yourself relax as Dean placed both of his hands on your shoulders and began massaging out the knots that had formed in them over the past few hours. He leaned over, his scruff scratching your cheek.

“How about you take a break, hm?” He whispered seductively, and you closed your eyes in attempt to maintain some form of self-control. _No, Y/N, you need to finish this paper,_ you said to yourself.

“Babe, I gotta finish this,” you groaned.

“How about some motivation then?” Dean asked, and you turned your head to look at him suspiciously.

“Yeah? Like what? You’re going to fuck me while I write my paper and not let me cum until I finish it?” You asked sarcastically. You regretted saying this as soon as you saw the lightbulb go off in Dean’s head. You had given him an idea, and judging by how fast he stopped rubbing your shoulders and made his way over to the door so he could lock it, he was 100% committed to it. You gulped as he walked back over to you, a different look in his eyes than the gentleness that had been there only moments before. He was in a different headspace now, one where he was in control and he was going to let you know it. At this point, your brain was fried and you were happy to hand over any and all decision making to Dean if it meant that you got to finish your paper and feel a release all at the same time.

“Keep working,” Dean ordered, and you turned back around to your laptop, trying to think of what to type next. You felt Dean behind you, his hands on your shoulders again, massaging them gently. You relaxed under his touch and began to type as an idea came to you. His hands moved to your front, slipping under your shirt and beginning to massage your breasts. You weren’t wearing a bra; you were still in your pajamas from the morning. You moaned and leaned your head back against Dean’s abdomen as he ran a finger over your hardening nipple. “Uh-uh, focus,” Dean said, as he bent over so his head was near your neck, taking away the comfortable headrest that had been his stomach. You let out a shaky breath as you tried to re-focus on your paper while Dean continued to relentlessly tease you under your shirt. He started kissing your neck and you tried to ignore him as best as you could, a few more sentences coming to you as you did so. Some way, somehow, this was actually clearing up the fog in your brain that had been keeping you from thinking of anything at all. You paused typing for a moment and Dean took the opportunity to slide you and your chair away from the desk, crawling under it and pulling both you and the chair back towards him by its legs. You knew exactly where this was headed, and you weren’t too confident in yourself that you could stay focused on your paper. Dean ran his hands up your legs, stopping when he got to the hem of your shorts. He tugged on them, and you lifted your ass so he could slide them off, along with your underwear. You shivered as the cool air met the growing heat in between your legs. _Concentrate_ , you remined yourself. You felt Dean spread your legs forcefully, running his hands along your thighs, his thumbs lightly massaging the inner parts. You cleared your throat in an attempt to make yourself focus on the words in front of you, typing out another sentence as you did so. You felt Dean’s hot breath near your core and you tried to pay no mind to the wetness that you could feel pooling between your legs. Dean began licking stripes up your folds, drawing a moan out of you. “It doesn’t sound like you’re very focused,” he said, flicking his tongue against your clit. You knew Dean meant this as a warning to you about making any more noise, so you began thinking about your paper as hard as you could. As Dean continued to eat you out, you continued to type paragraphs, the words just coming to you. You were caught off guard when you felt Dean’s fingers enter you, and it was only then that you stopped typing and let yourself feel him. His tongue moving masterfully between your folds, two of his fingers pumping in and out of you slowly, brushing up against your g-spot every time he pulled them almost all the way out, but not hitting it in a way that would send you over the edge. You glanced at how many pages you had written in the bottom left corner of your screen. Page 6 of 6. You only had two more to go and you knew that Dean wasn’t anywhere near done; you could afford yourself a moment to feel the pleasure that he was giving you. Or at least, you thought you could. “I don’t hear any typing,” Dean growled as he pulled his fingers out of you and pushed your chair back, standing up from under the desk. You whimpered at both the loss of him inside of you and the look on Dean’s face; you were in for it. “Stand up,” he commanded, and you quickly obeyed. “Bend over and keep typing,” he ordered as he stepped aside and motioned towards your desk. You quickly made your way over to your desk and bent over, your elbows resting on the hard surface as you wrote out another sentence. You heard the sound of a zipper behind you and your entrance clenched around nothing as it waited to be filled. _Focus, Y/N. Keep typing,_ you reminded yourself. You felt Dean’s presence behind you and he grabbed your hip with one hand, the other hand beginning to move his cock between your folds. You tried your best to focus on your paper, to keep typing, but your breath hitched in your throat as Dean slid into you, and you let yourself feel him fill you for a moment, closing your eyes and letting out a moan. Dean leaned over you and gripped your throat, his stubble rough against your ear. “If that paper’s not finished by the time I cum, you won’t be cumming for a week,” he growled, as he began to thrust into you. You began typing frantically; you didn’t even care if it made sense at this point, you just wanted to see “Page 8 of 8” appear in the corner so you could give your full attention over to the way that Dean was making you feel. You tried your best to ignore Dean’s pants and grunts as he thrusted into you, the hold he had on your throat making it extremely hard for you to look at your keyboard. You knew he was doing that on purpose. You were rocking back and forth on your elbows, which also was making it hard to type, but you continued pumping out paragraphs to the best of your ability. You refused to let yourself focus on anything but this paper, and it was working. Finally, you saw “Page 8 of 8” at the bottom of your screen. You saved the document and closed your laptop, never wanting to look at a computer screen again. You could focus on Dean now, on his cock inside of you, on his grunting, his moaning, the way he was saying “fuck” under his breath. Dean leaned in close to your ear again. “Did you finish?” You nodded to the best of your ability; his hand was still wrapped around your throat as he continued to ram into you mercilessly. “Good girl,” he whispered, his thrusts getting faster and rougher, causing you to moan in pleasure. Dean released the grip he had on your throat and grabbed your hips with both hands, digging his fingers into you as he sped up his thrusting. You could tell he was close; his thrusts were becoming sloppy and he wasn’t holding any noises back as he chased his climax.

“Fuck, Dean!” Was all you could manage to get out as he pounded into you at his hardest a few more times before you felt his warm cum fill you.

“That’s right, baby. Take it,” he panted as he grabbed you by your biceps and pushed himself into you as far as he could go. You let out a shaky breath as your legs turned into jelly; it was taking most of your strength to keep yourself from collapsing onto the floor. You were tired, your brain was absolutely fried, and all you wanted was to feel a release. Dean pulled out of you slowly and helped you stand up, keeping you steady as he walked you over to the bed. “Get comfortable, sweetheart,” he said, his demeanor changing from dominant to caring as he gave you a quick kiss on your forehead and walked over to your dresser. He knew where you kept your toys. You laid back against a pile of pillows at the head of your bed and spread your shaky legs. You watched Dean rummage through your dresser between them, his perfect body on display for you. _Why the hell can’t my ass look like that?_ You thought to yourself as you stared at your boyfriend’s ass. Why God decided to give men the things they didn’t need like long eyelashes and big butts was beyond you. You bit your lip as Dean turned around, a vibrator in one hand and a blindfold in the other. “You look so fucking hot with my cum spilling out of you,” he growled as he made his way over to the head of the bed, handing you the blindfold. “Put that on for me, I don’t want you focusing on anything but how good I’m about to make you feel.” You gave him a quick nod and slipped on the blindfold, falling into a darkness. Your other senses went into hyper-mode, trying to make up for the loss of one. You felt the mattress dip as Dean climbed onto the bed, making himself comfortable between your spread legs. You heard the vibrator turn on; the familiar buzzing like music to your ears. Your breath hitched in anticipation; you needed to be touched. Dean placed the vibrator on your inner thigh, slowly dragging it down your skin, stopping right before it reached where you needed it the most. He did the same with your other thigh, making you whine in frustration. “Patience, sweetheart.” _Easy for you to say, you didn’t just spend a million hours writing a stupid paper! Patience is not in my vocabulary right now,_ was what you wanted to say, but you settled for a nod instead; that was the much safer option. Dean moved the vibrator to one of your erect nipples, causing you to arch your back. You felt his hand press down gently on your abdomen, forcing you back down to the bed. “Stay still,” he ordered, a newfound gentleness to his voice. You took a deep breath and clenched every muscle in your body trying to stay still, and finally, Dean rewarded you by placing the vibrator right where you had been wanting it the most.

“Fuuuck,” you moaned, letting yourself feel the vibrations all throughout your body. Dean slipped two fingers inside of you and began moving them in and almost out of you as he changed the vibrator’s pattern to three short vibrations followed by a long one. He began fingering you in an alternate rhythm, making sure that if your clit wasn’t being stimulated, then your pussy was, and vice-versa. You focused on how good it felt, on how all the stress that you had been feeling was slowly disappearing. You relaxed completely, letting the heat in between your legs build, moaning obscenities as Dean made you feel the best you had felt in a long time. The familiar knot in your abdomen began forming, and you started to arch your back as you felt yourself about to let go. The heat that had risen in your core shot through you in waves and you moaned so loudly at the euphoric feeling that was making its way to every part of your body, that it could have easily been mistaken for a scream. You arched your back as a second shockwave of pleasure ran through you, and you could have sworn that for a split second you saw stars. Dean let you ride out your orgasm, your pussy clenching around his fingers as the feeling slowly faded. He turned the vibrator off and pulled his fingers out of you, leaning over you to take the blindfold off. You squeezed your eyes shut as the brightness of the room hit your pupils, and blinked a few times so your eyes could adjust to the light. You didn’t want to move. You were absolutely spent, thanks to both Dean and your paper, but you knew that you needed to shower. You looked at Dean with a sleepy and pouty look on your face, and he knew exactly what it meant.

“Do you need me to carry you to the shower?” He chuckled, as he placed the vibrator and blindfold at the foot of your bed. All you could do was nod and put your arms out in front of you; you did not have the energy to act like a functioning adult at the moment. Dean leaned over the bed and let you wrap your arms around his neck, grabbing you by your ass and lifting you off the bed, your legs wrapping around his waist. Sam was off with Eileen on a hunt, so Dean was able to carry you from your room to the bunker’s bathroom without worrying about anyone seeing the two of you. You nuzzled your face into Dean’s neck and let out a happy sigh. “Do you feel a little less stressed now?” Dean asked, as he opened the bathroom door and let you down on your feet.

“I don’t feel any stress at all. Thank you,” you said sweetly, looking up at the perfect man in front of you and giving him a kiss. “I love you.”

“I love you, too. Please take care of yourself, Y/N. That much stress is not good for you.”

You laughed at the irony of Dean Winchester saying this to you. “Alright, Mr. Save-The-World. For you, I’ll try to space out my homework.”


	2. Concentrate

**Summary for the Chapter:**

> After you get an awful grade back on the paper that Dean had "helped" you with, he has some other ways in mind to help you with your lack of concentration problem.

A week had passed since Dean had attempted to fuck the concentration into you, and you were nervous to see what you had received on your “sex paper” as you liked to call it. To be honest, you were so tired after the whole encounter than when you submitted it that night you didn’t even bother to look over it. You still hadn’t read over it; you were too scared to. You had always sucked at writing papers, and you had a gut feeling that this one, even though you had a fun time writing it, was not going to be any better than any of your others. Your professor released the grades in five minutes, and you were sitting in the bunker’s library, nervously biting at your fingernails while you waited for your result.

“Hey baby, whatchya up to?” Dean questioned as he walked into the library, giving you a quick kiss on the top of your head as he passed you.

“Waiting to see my grade on that damn paper,” you replied, your eyes set on your computer screen.

“The one I fuck –”

“Yes, that one,” you interrupted, before Dean could finish. He pulled out a book from one of the shelves and sat down next to you.

“You think you did good?”

“Not at all.”

“What? You mean the sex didn’t help you concentrate?”

“It helped me finish it! I just don’t know if what I wrote was at all coherent,” you explained, refreshing your page. Still no grade.

“Huh,” Dean huffed, as he opened the book in front of him.

“What?” You questioned.

“Oh, nothing. Just thinking.”

“Wanna elaborate?”

“Sure. If you end up getting a bad grade on that paper,” Dean began, “you won’t be able to sit for a week.”

You raised your eyebrows at him in surprise; he was never usually this upfront and bold about his dominant role outside of the bedroom – not that you were complaining. Hearing those words come out of his mouth sent a shiver down your spine as you felt a familiar heat rise in between your legs. “And if I get a good grade?” You asked.

“Then you won’t be able to walk for a week,” Dean shrugged, smirking as he skimmed over a page in the book.

“Sounds fair. You read now?” You questioned; you were usually used to seeing Sam do all the reading.

“Sam’s getting groceries, I’m trying to find us a hunt. I’m bored.”

You nodded in understanding as you clicked the refresh button on your screen, now more anxious than ever as you awaited your grade knowing that you were either going to get fucked or punished depending on the result. Dean paused his skimming to look at your screen with you as it loaded. Your stomach churned as you saw a 67% appear in red text near the “grade” section of your course page. Dean sucked in through his teeth.

“That’s rough,” he stated simply, adding a cocky smirk and raising his eyebrows playfully before going back to his book. Cheeky bastard was excited. You sighed.

“I thought I at least did better than that,” you groaned, closing your laptop and resting your head on the table in front of you.

“Sorry, sweetheart,” Dean said as he closed the book and put it back on the shelf. You assumed he found the information he needed. “Looks like I’m going to have to remind you how to concentrate.”

* * *

“Ready?” Dean asked. You were over his knee in your bedroom; Dean was sitting on the edge of the bed that the two of you often shared and your upper body was resting on the mattress as your legs were trapped in between Dean’s thighs. You figured this is what he meant by “you won’t be able to sit for a week”. You squeezed your thighs together, trying to give your core some friction; you were rarely ever this wet. Something about Dean being so out and open with his dominance turned you on more than usual. You had received a lot of bad grades in the time that the two of you had been together and he had never punished you for it, but _fuck_ , if it wasn’t the hottest thing you had ever experienced. You nodded in response to Dean’s question, earning you a firm smack on your upper thigh; a part of you that wasn’t covered by a layer of jean shorts and cotton underwear. “C’mon, Y/N. Let’s not slip up yet; we haven’t even started. I’ll ask again. Are you ready?” You took a deep breath as you tried to ignore the overwhelming heat between your legs.

“Yes, sir,” you replied, bracing yourself for the first hit. When Dean said that he was going to remind you how to concentrate, this is the little exercise he had in mind. “I’m gonna spank you, and you’re gonna count”, he had said nonchalantly. You tried to ask him how high you’d be counting, to which he replied, “until my arm gets tired”. It was in this moment that you realized how absolutely fucked you were; it took quite a bit to tire out any part of Dean.

“Remember, if you lose count, we’re starting over. So, _concentrate_ ,” he added, before the first smack hit your denim-clad ass. You knew you weren’t going to have the protection of the fabric for long, but until then you were thankful for the barrier that it provided.

“One,” you counted, loud enough so Dean couldn’t retort with some BS “I can’t hear you” statement and make you start over. You weren’t playing that game tonight. It’s not that you didn’t absolutely love being over Dean’s knee, your spanking kink was something else, but you knew that you’d be here long enough already and you were so wet that the quicker you could get to the part where you felt a release, the better. You felt Dean’s hand come down on your ass again. “Two.”

“These are getting in my way,” Dean huffed as he reached under you to unbutton your shorts and shimmied them down to your knees. _Well, those didn’t last nearly as long as I thought they would_ , you thought to yourself. With only a thin cotton layer protecting you now, you were in for it. You winced as the next hit came down, really feeling the sting without the denim to protect you.

“Three,” you counted, trying your best to keep your voice from wavering. Another hit. “Four.” And another. “Five.” Dean rained down swats as you tried to keep up counting-wise, the heat really starting to come off of your ass now. “Twelve!” You yelped, really feeling the sting of that one. Dean paused his hits and you knew you had fucked up.

“What number was that?” Dean questioned, making sure he heard you right.

“Eleven,” you whispered.

“But that’s not what you said, is it?”

“No, sir,” you murmured. Dean took the opportunity to slide your panties down, meeting your denim shorts which were still at your knees. _Fuck._

“Alright, start over,” he said plainly, as though he could sit here and do this all fucking day. You obeyed, focusing on nothing but the stinging swats that were being delivered to your bare ass with Dean’s large calloused hand. This was where this little scenario became both a punishment for the bad grade and an exercise to help you concentrate; you couldn’t focus on anything but the stinging hits, in attempt to not miscount them again, which means you couldn’t think about something else when the spanking crossed the line from pleasurable pain to somewhat painful. This game of concentration was forcing you to feel every hit, no matter how hard, and you weren’t sure if you hated it or loved it. Your pussy was all for it, but your brain… your brain wasn’t the best at focusing. You couldn’t say how many times you’d slipped into a daydream in the middle of a punishment; you couldn’t help it most of the time. It was also why you sucked at writing essays and doing anything else that involved concentrating for a long period of time. You had the attention span of a fly, and it wasn’t your fault; it was just how your brain was wired for the most part. It didn’t mean that you couldn’t work on that concentration, like you were doing now in a most unconventional way with Dean, but it did mean that you weren’t going to like working on it. You assumed Dean knew all of this, which is why this is the punishment he had picked; it was perfect for you. You had counted thirty-nine at this point, and your ass was on fire, as was the heat in between your legs. You lunged forward as another hit came down and yelped, “Forty!” _Please, let that be the last one._ You genuinely didn’t know if you could take any more; you crossed the somewhat painful threshold about 20 hits ago. Dean paused to rub circles on your bare ass with his palm, providing some much-needed relief. You allowed yourself to relax as Dean inched his hand closer to your folds, letting you know that he was done. It wasn’t the worst punishment you had received; the number may have been high but he stuck to his hand, so the pain could have been far worse. You heard Dean let air out through his nose as a smirk probably formed on his lips. He was exploring your folds with his fingers now, spreading your juices around them. You hated how wet you were from this alone. “It seems like you enjoy your punishments too much,” Dean chuckled as he continued to play with your pussy.

“Trust me, it was psychologically grueling,” you assured him, letting him know that the addition of counting was a nice touch. “And on top of that, I definitely won’t be able to sit properly for a week.”

“Yeah, that does seem like it’s gonna be the case.” Dean brought his hand back to rub your ass a bit more, soothing the tingling sensation that was still coming off of it. “You ready for the next part?” Your eyes grew wide.

“What?” You squeaked.

“Oh, c’mon, Y/N. You failed that paper… miserably. After I thought I did a pretty good job at helping you concentrate on it. Plus, I know how much you love being over my knee, so you can’t possibly think that that was it,” Dean stated. You took a deep breath. If this wasn’t going to make you at least think about concentrating harder, you didn’t know what was. “Get undressed, lay on the bed. On your back,” Dean commanded, releasing you from between his thighs and helping you stand. He got up from the bed and walked over to the dresser. You had absolutely no idea what was coming next, and the anticipation only made your clit pulse. You made yourself comfortable on the bed, your back resting against a pile of pillows. You watched Dean between the gap in your spread legs as he pulled out your vibrator from the dresser, the scene very similar to the one from last week. Except, last week Dean’s main goal was to de-stress you after you finished your paper, and this week… well, this week it was to punish you for not writing your paper to the best of your ability. He was fucking the life out of you at the time of you writing it; how could he blame you for that one? You rolled your eyes at the thought, thankful that Dean was still turned around because Lord only knows what trouble you’d be in if he saw the expression. Dean walked over to you and got onto the bed in between your legs; the same position he was in last week although with a totally different goal in mind. “Do not move. Do not make a sound. And do not cum until I say so,” he ordered in a husky tone. You gulped and nodded; oh, how you hated him right now. Dean wasted no time placing the vibrator directly on your throbbing clit, a moan nearly escaping your lips before you remembered to concentrate on staying still and silent. Another fucked up concentration exercise forged in the darkest parts of Dean’s mind. Dean leaned forward and pinched your hardened nipple between his fingers and you squeezed every muscle in your body as you tried to remain still. He was relentless, just as he had been earlier when you were over his knee, just as he had been last week when he was fucking you senseless while you were writing your paper. You took a few deep breaths as you tried to concentrate on anything but the pleasurable vibrations that you were feeling throughout your body. Your core was aching to be filled and you assumed Dean knew this judging by the fact that two of his fingers entered you with no warning. You almost let out a gasp, but you held it in. “Good girl,” Dean purred, his praise causing your pussy to clench around his fingers. He started to pump them slowly, scissoring and curling them at all the right spots. You wanted him buried inside you so bad, but you knew that asking would only prove to Dean how much you weren’t concentrating at the task at hand; staying still and keeping quiet. You were close to a release, you could feel the coil in your abdomen begin to form as Dean continued to finger fuck you, holding the vibrator in place on your clit. You tensed up as you tried to keep the coil from snapping, the heat at your core almost unbearable as you kept your orgasm at bay. “Hold it. Concentrate,” Dean ordered, not that it helped. His domineering tone only brought you closer to the edge. You squeezed your eyes shut, holding back your pleasure. You only had about 10 seconds left in you before you’d have to let yourself cum. All you had to hear were those magic words from Dean’s lips. Five, four – _fuck, Dean, please_ – you thought. Three, two, “Alright, cum for me, sweetheart,” Dean finally said. You felt the coil in you snap and you tried to do your best to stay still and silent throughout the wave of pleasure that was washing over you. You only squirmed a little and let out a pant or two, which, from what you could tell by the approving smirk he had on his face, Dean was very impressed with. “See? A little concentration goes a long way,” he hummed, turning off the vibrator and throwing it somewhere on the mattress. You smiled at him playfully, figuring that it’d be safe to speak now.

“Can I concentrate on you, now?” You asked innocently. Dean chuckled and practically threw himself on top of you, holding himself over you with his arms on either side of your shoulders.

“You’re even _asking_ to concentrate? I love it when my punishments work,” he said with a cocky smile, to which you held back an eye roll; you didn’t want to test the waters with that one just yet. You wrapped your hands around his neck and pulled him in for a kiss. He moaned as you reached down with one hand to palm the erection that was growing under his jeans and he flipped you over so you were now straddling him in one swift motion. You wasted no time as you scooted to the bottom of the bed, your face hovering above his fly as you unbuttoned his jeans. You looked up at him through your eyelashes, his lips parted in anticipation as he watched you pull his hardened cock out from beneath the cotton and denim layers. You teased him by licking a few stripes up his shaft, before taking all of him in your mouth. Dean let out a guttural moan followed by a “fuck” which made you grab his cock at the base and lift your head off of it so you could look him in the eyes.

“Be quiet, baby. All that noise makes it hard for me to concentrate.”


End file.
